JEE Main Chemistry question

Chemistry Organic Chemistry - Some Basic Principles and Techniques JEE Main

[IIT 1995] Among the benzylic cations *p*-O₂N–C₆H₄–CH₂⁺, C₆H₅–CH₂⁺, *p*-Cl–C₆H₄–CH₂⁺ and *p*-CH₃O–C₆H₄–CH₂⁺, the most stable is

(A)*p*-O₂N–C₆H₄–CH₂⁺ (destabilised by the EWG)
(B)C₆H₅–CH₂⁺ (unsubstituted benzylic cation)
(C)*p*-Cl–C₆H₄–CH₂⁺ (net destabilised; Cl's –I outweighs its weak +R at this distance)
(D)*p*-CH₃O–C₆H₄–CH₂⁺Correct

Answer: (D)

Solution

The *para*-methoxy group donates its oxygen lone pair directly into the ring by resonance, delocalising positive charge onto oxygen and strongly stabilising the

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Question ID VK-140391